Liquid crystal composition and liquid crystal display device

ABSTRACT

Provided is a liquid crystal composition satisfying at least one of characteristics such as a high maximum temperature, a low minimum temperature, small viscosity, large optical anisotropy and large dielectric anisotropy, or has a suitable balance regarding at least two of the characteristics, and an AM device including the composition. The liquid crystal composition may contain a specific compound having large negative dielectric anisotropy as a first component, a specific compound having a high maximum temperature or small viscosity as a second component, a specific compound having negative dielectric anisotropy as a third component, or a specific compound having a polymerizable group as an additive component.

TECHNICAL FIELD

The invention relates to a liquid crystal composition, a liquid crystaldisplay device including the composition, and so forth. In particular,the invention relates to a liquid crystal composition having a negativedielectric anisotropy, and a liquid crystal display device that includesthe composition and has a mode such as an IPS mode, a VA mode, an FFSmode and an FPA mode. The invention also relates to a liquid crystaldisplay device having a polymer sustained alignment mode.

BACKGROUND ART

In a liquid crystal display device, a classification based on anoperating mode for liquid crystal molecules includes a phase change (PC)mode, a twisted nematic (TN) mode, a super twisted nematic (STN) mode,an electrically controlled birefringence (ECB) mode, an opticallycompensated bend (OCB) mode, an in-plane switching (IPS) mode, avertical alignment (VA) mode, a fringe field switching (FFS) mode and afield-induced photo-reactive alignment (FPA) mode. A classificationbased on a driving mode in the device includes a passive matrix (PM) andan active matrix (AM). The PM is classified into static, multiplex andso forth, and the AM is classified into a thin film transistor (TFT), ametal insulator metal (MIM) and so forth. The TFT is further classifiedinto amorphous silicon and polycrystal silicon. The latter is classifiedinto a high temperature type and a low temperature type based on aproduction process. A classification based on a light source includes areflective type utilizing natural light, a transmissive type utilizingbacklight and a transflective type utilizing both the natural light andthe backlight.

The liquid crystal display device includes a liquid crystal compositionhaving a nematic phase. The composition has suitable characteristics. AnAM device having good characteristics can be obtained by improvingcharacteristics of the composition. Table 1 below summarizes arelationship in two characteristics. The characteristics of thecomposition will be further described based on a commercially availableAM device. A temperature range of the nematic phase relates to atemperature range in which the device can be used. A preferred maximumtemperature of the nematic phase is about 70° C. or higher, and apreferred minimum temperature of the nematic phase is about −10° C. orlower. Viscosity of the composition relates to a response time of thedevice. A short response time is preferred for displaying moving imageson the device. A shorter response time even by one millisecond isdesirable. Accordingly, a small viscosity of the composition ispreferred. A small viscosity at a low temperature is further preferred.

TABLE 1 Characteristics of Composition and AM Device No. Characteristicsof Composition Characteristics of AM Device 1 Wide temperature range ofa Wide usable temperature range nematic phase 2 Small viscosity Shortresponse time 3 Suitable optical anisotropy Large contrast ratio 4 Largepositive or negative Low threshold voltage and dielectric anisotropysmall electric power consump- tion Large contrast ratio 5 Large specificresistance Large voltage holding ratio and large contrast ratio 6 Highstability to ultraviolet light Long service life and heat

An optical anisotropy of the composition relates to a contrast ratio inthe device. According to a mode of the device, a large opticalanisotropy or a small optical anisotropy, more specifically, a suitableoptical anisotropy is required. A product (Δn×d) of the opticalanisotropy (An) of the composition and a cell gap (d) in the device isdesigned so as to maximize the contrast ratio. A suitable value of theproduct depends on a type of the operating mode. In a device having theVA mode, the suitable value is in the range of about 0.30 micrometer toabout 0.40 micrometer, and in a device having the IPS mode or the FFSmode, the suitable value is in the range of about 0.20 micrometer toabout 0.30 micrometer. In the above cases, a composition having thelarge optical anisotropy is preferred for a device having a small cellgap. A large dielectric anisotropy in the composition contributes to alow threshold voltage, a small electric power consumption and a largecontrast ratio in the device. Accordingly, the large dielectricanisotropy is preferred. A large specific resistance in the compositioncontributes to a large voltage holding ratio and the large contrastratio in the device. Accordingly, a composition having the largespecific resistance at room temperature and also at a temperature closeto the maximum temperature of the nematic phase in an initial stage ispreferred. The composition having the large specific resistance at roomtemperature and also at a temperature close to the maximum temperatureof the nematic phase even after the device has been used for a longperiod of time is preferred. Stability of the composition to ultravioletlight and heat relates to a service life of the device. In the casewhere the stability is high, the device has a long service life. Suchcharacteristics are preferred for an AM device used in a liquid crystalprojector, a liquid crystal television and so forth.

In a liquid crystal display device having a polymer sustained alignment(PSA) mode, a liquid crystal composition containing a polymer is used.First, a composition to which a small amount of a polymerizable compoundis added is injected into the device. Then, the composition isirradiated with ultraviolet light while voltage is applied betweensubstrates of the device. The polymerizable compound is polymerized toforma network structure of the polymer in the composition. In thecomposition, alignment of liquid crystal molecules can be controlled bythe polymer, and therefore the response time of the device is shortenedand also image persistence is improved. Such an effect of the polymercan be expected for a device having the mode such as the TN mode, theECB mode, the OCB mode, the IPS mode, the VA mode, the FFS mode and theFPA mode.

A composition having positive dielectric anisotropy is used in an AMdevice having the TN mode. A composition having negative dielectricanisotropy is used in an AM device having the VA mode. A compositionhaving positive or negative dielectric anisotropy is used in an AMdevice having the IPS mode or the FFS mode. In an AM device havingpolymer sustained alignment mode, a composition having positive ornegative dielectric anisotropy is used. Example of a first component inthe invention is disclosed in Patent literature No. 1 described below.

CITATION LIST Patent Literature

Patent literature No. 1: JP 2000-328062 A.

SUMMARY OF INVENTION Technical Problem

One of aims of the invention is to provide a liquid crystal compositionsatisfying at least one of characteristics such as a high maximumtemperature of a nematic phase, a low minimum temperature of the nematicphase, a small viscosity, a suitable optical anisotropy, a largenegative dielectric anisotropy, a large specific resistance, a highstability to ultraviolet light and a high stability to heat. Another aimis to provide a liquid crystal composition having a suitable balanceregarding at least two of the characteristics. Another aim is to providea liquid crystal display device including such a composition. Anotheraim is to provide an AM device having characteristics such as a shortresponse time, a large voltage holding ratio, a low threshold voltage, alarge contrast ratio and a long service life.

Solution to Problem

The invention concerns a liquid crystal composition that has a nematicphase and a negative dielectric anisotropy, and contains at least onecompound selected from the group of compounds represented by formula (1)as a first component, and a liquid crystal display device including thecomposition:

wherein, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring A and ring B are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, or1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine; naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine; Z¹ and Z² areindependently a single bond, ethylene, carbonyloxy or methyleneoxy; aand b are independently 0, 1, 2 or 3; and a sum of a and b is 4 or less.

Advantageous Effects of Invention

One of advantage of the invention is a liquid crystal compositionsatisfying at least one of characteristics such as a high maximumtemperature of a nematic phase, a low minimum temperature of the nematicphase, a small viscosity, a large optical anisotropy, a large negativedielectric anisotropy, a large specific resistance, a high stability toultraviolet light and a high stability to heat. Another advantage is aliquid crystal composition having a suitable balance regarding at leasttwo of the characteristics. Another advantage is a liquid crystaldisplay device including such a composition. Another advantage is an AMdevice having characteristics such as a short response time, a largevoltage holding ratio, a low threshold voltage, a large contrast ratioand a long service life.

DESCRIPTION OF EMBODIMENTS

Usage of terms herein is as described below. Terms “liquid crystalcomposition” and “liquid crystal display device” may be occasionallyabbreviated as “composition” and “device,” respectively. “Liquid crystaldisplay device” is a generic term for a liquid crystal display panel anda liquid crystal display module. “Liquid crystal compound” is a genericterm for a compound having a liquid crystal phase such as a nematicphase and a smectic phase, and a compound having no liquid crystal phasebut to be mixed with a composition for the purpose of adjustingcharacteristics such as a temperature range of the nematic phase,viscosity and a dielectric anisotropy. The compound has a six-memberedring such as 1,4-cyclohexylene and 1,4-phenylene, and has rod-likemolecular structure. “Polymerizable compound” is a compound to be addedfor the purpose of forming a polymer in the composition.

The liquid crystal composition is prepared by mixing a plurality ofliquid crystal compounds. A proportion (content) of the liquid crystalcompounds is expressed in terms of weight percent (% by weight) based onthe total amount of the liquid crystal composition. An additive such asan optically active compound, an antioxidant, an ultraviolet lightabsorber, a dye, an antifoaming agent, the polymerizable compound, apolymerization initiator and a polymerization inhibitor is added to thecomposition when necessary. A proportion (amount of addition) of theadditive is expressed in terms of weight percent (% by weight) based onthe total amount of the liquid crystal composition in a manner similarto the proportion of the liquid crystal compounds. Weight parts permillion (ppm) may be occasionally used. A proportion of thepolymerization initiator and the polymerization inhibitor isexceptionally expressed based on the total amount of the polymerizablecompound.

“Maximum temperature of the nematic phase” may be occasionallyabbreviated as “maximum temperature.” “Minimum temperature of thenematic phase” may be occasionally abbreviated as “minimum temperature.”An expression “having a large specific resistance” means that thecomposition has a large specific resistance at room temperature and alsoat a temperature close to the maximum temperature of the nematic phasein an initial stage, and the composition has the large specificresistance at room temperature and also at a temperature close to themaximum temperature of the nematic phase even after the device has beenused for a long period of time. An expression “having a large voltageholding ratio” means that the device has a large voltage holding ratioat room temperature and also at a temperature close to the maximumtemperature of the nematic phase in the initial stage, and the devicehas the large voltage holding ratio at room temperature and also at atemperature close to the maximum temperature of the nematic phase evenafter the device has been used for the long period of time. Anexpression “increase the dielectric anisotropy” means that a value ofdielectric anisotropy positively increases in a liquid crystalcomposition having a positive dielectric anisotropy, and the value ofdielectric anisotropy negatively increases in a liquid crystalcomposition having a negative dielectric anisotropy.

A compound represented by formula (1) may be occasionally abbreviated as“compound (1).” At least one compound selected from the group ofcompounds represented by formula (2) may be occasionally abbreviated as“compound (2).” “Compound (1)” means one compound, a mixture of twocompounds or a mixture of three or more compounds represented by formula(1). A same rule applies also to any other compound represented by anyother formula. An expression “at least one piece of ‘A’” means that thenumber of ‘A’ is arbitrary. An expression “at least one piece of ‘A’ maybe replaced by ‘B’” means that, when the number of ‘A’ is 1, a positionof ‘A’ is arbitrary, and also when the number of ‘A’ is 2 or more,positions thereof can be selected without restriction. A same ruleapplies also to an expression “at least one piece of ‘A’ is replaced by‘B’.”

A symbol of terminal group R¹ is used in a plurality of compounds inchemical formulas of component compounds. In the compounds, two groupsrepresented by two pieces of arbitrary R¹ may be identical or different.For example, in one case, R¹ of compound (1-1) is ethyl and R¹ ofcompound (1-2) is ethyl. In another case, R¹ of compound (1-1) is ethyland R¹ of compound (1-2) is propyl. A same rule applies also to a symbolof any other terminal group or the like. In formula (3), when d is 2,two of rings E exists. In the compound, two rings represented by two ofrings E may be identical or different. A same rule applies also to twoof arbitrary rings E when d is larger than 2. A same rule applies alsoto a symbol of Z¹, ring A or the like. A same rule applies also to sucha case where two pieces of -Sp²-P⁵ exists in compound (4-27).

Symbols A, B, C or the like surrounded by a hexagonal shape correspondto six-membered rings such as ring A, ring B and ring C, respectively.In compound (4), a hexagon shape represents a six-membered ring or acondensed ring. An oblique line crossing the hexagonal shape representsthat arbitrary hydrogen on the ring may be replaced by -Sp¹-P¹ group orthe like. A subscript such as g represents the number of groups to bereplaced. When the subscript is 0, no such replacement exists. When g is2 or more, a plurality of pieces of -Sp¹-P¹ exist on ring I. Theplurality of groups represented by -Sp¹-P¹ may be identical ordifferent.

Then, 2-fluoro-1,4-phenylene means two divalent groups described below.In a chemical formula, fluorine may be leftward (L) or rightward (R). Asame rule applies also to an asymmetrical divalent group derived from aring such as tetrahydropyran-2,5-diyl. A same rule applies also to adivalent bonding group such as carbonyloxy (—COO— or —OCO—).

The invention includes items described below.

Item 1. A liquid crystal composition that has a nematic phase and anegative dielectric anisotropy, and contains at least one compoundselected from the group of compounds represented by formula (1) as afirst component:

wherein, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring A and ring B are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine; Z¹ and Z² areindependently a single bond, ethylene, carbonyloxy or methyleneoxy; aand b are independently 0, 1, 2 or 3; and a sum of a and b is 4 or less.

Item 2. The liquid crystal composition according to item 1, containingat least one compound selected from the group of compounds representedby formula (1-1) to formula (1-12) as the first component:

wherein, in formula (1-1) to formula (1-12), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.

Item 3. The liquid crystal composition according to item 1 or 2, whereina proportion of the first component is in the range of 3% by weight to30% by weight based on the total amount of the liquid crystalcomposition.

Item 4. The liquid crystal composition according to any one of items 1to 3, containing at least one compound selected from the group ofcompounds represented by formula (2) as a second component:

wherein, in formula (2), R³ and R⁴ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkyl having 1 to 12 carbons in which at least one piece ofhydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring C and ring D are independently 1,4-cyclohexylene,1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z³is a single bond, ethylene or carbonyloxy; and c is 1, 2 or 3.

Item 5. The liquid crystal composition according to any one of items 1to 4, containing at least one compound selected from the group ofcompounds represented by formula (2-1) to formula (2-13) as the secondcomponent:

wherein, in formula (2-1) to formula (2-13), R³ and R⁴ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkyl having 1 to 12 carbons in which at leastone piece of hydrogen is replaced by fluorine or chlorine, or alkenylhaving 2 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.

Item 6. The liquid crystal composition according to item 4 or 5, whereina proportion of the second component is in the range of 15% by weight to80% by weight based on the total amount of the liquid crystalcomposition.

Item 7. The liquid crystal composition according to any one of items 1to 6, containing at least one compound selected from the group ofcompounds represented by formula (3) as a third component:

wherein, in formula (3), R⁵ and R⁶ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring E and ring G are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine; ring F is2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene,2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl, or 7,8-difluorochroman-2,6-diyl; Z⁴and Z⁵ are independently a single bond, ethylene, carbonyloxy ormethyleneoxy; d is 1, 2 or 3; e is 0 or 1; and a sum of d and e is 3 orless.

Item 8. The liquid crystal composition according to any one of items 1to 7, containing at least one compound selected from the group ofcompounds represented by formula (3-1) to formula (3-22) as the thirdcomponent:

wherein, in formula (3-1) to formula (3-22), R⁵ and R⁶ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.

Item 9. The liquid crystal composition according to item 7 or 8, whereina proportion of the third component is in the range of 10% by weight to80% by weight based on the total amount of the liquid crystalcomposition.

Item 10. The liquid crystal composition according to anyone of items 1to 9, containing at least one polymerizable compound selected from thegroup of compounds represented by formula (4) as an additive component:

wherein, in formula (4), ring I and ring K are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, atleast one piece of hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one piece of hydrogen is replaced byfluorine or chlorine; ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthe rings, at least one piece of hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one piece of hydrogenis replaced by fluorine or chlorine; Z⁶ and Z⁷ are independently asingle bond or alkylene having 1 to 10 carbons, and in the alkylene, atleast one piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—,and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—,—C(CH₃)═CH—, —CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in the groups, at leastone piece of hydrogen may be replaced by fluorine or chlorine; P¹, P²and P³ are independently a polymerizable group; Sp¹, Sp² and Sp³ areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or —C≡C—, and in the groups, at least one piece of hydrogen maybe replaced by fluorine or chlorine; f is 0, 1 or 2; g, h and i areindependently 0, 1, 2, 3 or 4; and a sum of g, h and i is 1 or more.

Item 11. The liquid crystal composition according to item 10, wherein,in formula (4), P¹, P² and P³ are independently a polymerizable groupselected from the group of groups represented by formula (P-1) toformula (P-6):

wherein, in formula (P-1) to formula (P-6), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine;in formula (4), when all of g pieces of P¹ and i pieces of P³ are thegroup represented by formula (P-4), at least one piece of g pieces ofSp¹ and i pieces of Sp^(a) is alkylene in which at least one piece of—CH₂— is replaced by —O—, —COO—, —OCO— or —OCOO—.

Item 12. The liquid crystal composition according to anyone of items 1to 11, containing at least one polymerizable compound selected from thegroup of compounds represented by formula (4-1) to formula (4-27) as theadditive component:

wherein, in formula (4-1) to formula (4-27), P⁴, P⁵ and P⁶ areindependently a polymerizable group selected from the group of groupsrepresented by formula (P-1) to formula (P-3);

wherein, in formula (P-1) to formula (P-3), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine; andin formula (4-1) to formula (4-27), Sp¹, Sp² and Sp³ are independently asingle bond or alkylene having 1 to 10 carbons, and in the alkylene, atleast one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or —OCOO—,and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH— or —C≡C—,and in the groups, at least one piece of hydrogen may be replaced byfluorine or chlorine.

Item 13. The liquid crystal composition according to anyone of items 10to 12, wherein a proportion of the additive component is the range of0.03% by weight to 10% by weight based on the total amount of the liquidcrystal composition.

Item 14. A liquid crystal display device, including the liquid crystalcomposition according to any one of items 1 to 13.

Item 15. The liquid crystal display device according to item 14, whereinan operating mode in the liquid crystal display device includes an IPSmode, a VA mode, an FFS mode or an FPA mode, and a driving mode in theliquid crystal display device includes an active matrix mode.

Item 16. A polymer sustained alignment mode liquid crystal displaydevice, wherein the liquid crystal display device includes the liquidcrystal composition according to any one of items 1 to 13, or thepolymerizable compound in the liquid crystal composition is polymerized.

Item 17. Use of the liquid crystal composition according to any one ofitems 1 to 13 in a liquid crystal display device.

Item 18. Use of the liquid crystal composition according to any one ofitems 1 to 13 in a polymer sustained alignment mode liquid crystaldisplay device.

The invention further includes the following items: (a) the composition,further containing at least one of additives such as an optically activecompound, an antioxidant, an ultraviolet light absorber, a dye, anantifoaming agent, a polymerizable compound, a polymerization initiatoror a polymerization inhibitor; (b) an AM device including thecomposition; (c) the composition further containing a polymerizablecompound, and a polymer sustained alignment (PSA) mode AM deviceincluding the composition; (d) a polymer sustained alignment (PSA) modeAM device, wherein the device includes the composition, and apolymerizable compound in the composition is polymerized; (e) a deviceincluding the composition and having the PC mode, the TN mode, the STNmode, the ECB mode, the OCB mode, the IPS mode, the VA mode, the FFSmode or the FPA mode; (f) a transmissive device including thecomposition; (g) use of the composition as the composition having thenematic phase; and (h) use as an optically active composition by addingthe optically active compound to the composition.

The composition of the invention will be described in the followingorder. First, a constitution of the component compounds in thecomposition will be described. Second, main characteristics of thecomponent compounds and main effects of the compounds on the compositionwill be described. Third, a combination of components in thecomposition, a preferred proportion of the components and the basisthereof will be described. Fourth, a preferred embodiment of thecomponent compounds will be described. Fifth, a preferred componentcompounds will be described. Sixth, an additive that may be added to thecomposition will be described. Seventh, methods for synthesizing thecomponent compounds will be described. Last, an application of thecomposition will be described.

First, the constitution of the component compounds in the compositionwill be described. The composition of the invention is classified intocomposition A and composition B. Composition A may further contain anyother liquid crystal compound, an additive or the like in addition tothe liquid crystal compound selected from compound (1), compound (2),compound (3) and compound (4). An expression “any other liquid crystalcompound” means a liquid crystal compound different from compound (1),compound (2), compound (3) and compound (4). Such a compound is mixedwith the composition for the purpose of further adjusting thecharacteristics. The additive is the optically active compound, theantioxidant, the ultraviolet light absorber, the dye, the antifoamingagent, the polymerizable compound, the polymerization initiator, thepolymerization inhibitor or the like.

Composition B consists essentially of liquid crystal compounds selectedfrom compound (1), compound (2), compound (3) and compound (4). Anexpression “essentially” means that the composition may contain theadditive, but contains no any other liquid crystal compound. CompositionB has a smaller number of components than composition A has. CompositionB is preferred to composition A in view of cost reduction. Composition Ais preferred to composition B in view of possibility of furtheradjusting the characteristics by mixing any other liquid crystalcompound.

Second, the main characteristics of the component compounds and the maineffects of the compounds on the characteristics of the composition willbe described. The main characteristics of the component compounds aresummarized in Table 2 on the basis of advantageous effects of theinvention. In Table 2, a symbol L stands for “large” or “high,” a symbolM stands for “medium” and a symbol S stands for “small” or “low.” Thesymbols L, M and S represent a classification based on a qualitativecomparison among the component compounds, and 0 (zero) means that “avalue is zero” or “a value close to zero.”

TABLE 2 Characteristic of Compounds Compounds Compound (1) Compound (2)Compound (3) Maximum temperature M to L S to L S to L Viscosity M to L Sto M M to L Optical anisotropy M to L S to L M to L Dielectricanisotropy M to L¹⁾ 0 M to L¹⁾ Specific resistance L L L ¹⁾A value ofdielectric anisotropy is negative, and the symbol shows magnitude of anabsolute value.

Upon mixing the component compounds with the composition, the maineffects of the component compounds on the characteristics of thecomposition are as described below. Compound (1) increases thedielectric anisotropy. Compound (2) increases the maximum temperature ordecreases the viscosity. Compound (3) increases the dielectricanisotropy and decreases the minimum temperature. Compound (4) arepolymerized to give a polymer, and the polymer shortens a response timeof the device, and improves image persistence.

Third, the combination of components in the composition, the preferredproportion of the component compounds and the basis thereof will bedescribed. A preferred combination of components in the compositionincludes a combination of the first component and the second component,a combination of the first component, the second component and the thirdcomponent, a combination of the first component, the second componentand the additive component, a combination of the first component, thesecond component, the third component and the additive component. Afurther preferred combination of components includes a combination ofthe first component, the second component and the third component, acombination of the first component, the second component, the thirdcomponent and the additive component.

A preferred proportion of the first component is about 3% by weight ormore for increasing the dielectric anisotropy, and about 30% by weightor less for decreasing the viscosity. A further preferred proportion isin the range of about 3% by weight to about 20% by weight. Aparticularly preferred proportion is in the range of about 3% by weightto about 15% by weight.

A preferred proportion of the second component is about 15% by weight ormore for increasing the maximum temperature or decreasing the viscosity,and about 80% by weight or less for increasing the dielectricanisotropy. A further preferred proportion is in the range of about 25%by weight to about 70% by weight. A particularly preferred proportion isin the range of about 30% by weight to about 60% by weight.

A preferred proportion of the third component is about 10% by weight ormore for increasing the dielectric anisotropy, and about 80% by weightor less for decreasing the minimum temperature. A further preferredproportion is in the range of about 25% by weight to about 70% byweight. A particularly preferred proportion is in the range of about 30%by weight to about 65% by weight.

Compound (4) is added to the composition for the purpose of adapting thecomposition to the polymer sustained alignment mode device. A preferredproportion of the additive component is about 0.03% by weight or morefor aligning the liquid crystal molecules, and about 10% by weight orless for preventing poor display in the device. A further preferredproportion is in the range of about 0.1% by weight to about 2% byweight. A particularly preferred proportion is in the range of about0.2% by weight to about 1.0% by weight.

Fourth, the preferred embodiment of the component compounds will bedescribed. In formula (1), formula (2), formula (3) and formula (4), R¹,R², R⁵ and R⁶ are independently alkyl having 1 to 12 carbons, alkoxyhaving 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxyhaving 2 to 12 carbons, or alkyl having 1 to 12 carbons in which atleast one piece of hydrogen is replaced by fluorine or chlorine.Preferred R¹, R², R⁵ or R⁶ is alkyl having 1 to 12 carbons forincreasing the stability, and alkoxy having 1 to 12 carbons forincreasing the dielectric anisotropy. R³ and R⁴ are independently alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2to 12 carbons, alkyl having 1 to 12 carbons in which at least one pieceof hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to12 carbons in which at least one piece of hydrogen is replaced byfluorine or chlorine. Preferred R³ or R⁴ is alkenyl having 2 to 12carbons for decreasing the viscosity, and alkyl having 1 to 12 carbonsfor increasing the stability. Alkyl is straight-chain alkyl orbranched-chain alkyl, but includes no cyclic alkyl. Straight-chain alkylis preferred to branched-chain alkyl. A same rule applies also to aterminal group such as alkoxy and alkenyl.

Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptylor octyl. Further preferred alkyl is ethyl, propyl, butyl, pentyl orheptyl for decreasing the viscosity.

Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy,hexyloxy or heptyloxy. Further preferred alkoxy is methoxy or ethoxy fordecreasing the viscosity.

Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl. Furtherpreferred alkenyl is vinyl, 1-propenyl, 3-butenyl or 3-pentenyl fordecreasing the viscosity. A preferred configuration of —CH═CH— in thealkenyl depends on a position of a double bond. Trans is preferred inalkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyland 3-hexenyl for decreasing the viscosity, for instance. Cis ispreferred in alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.

Specific examples of preferred alkyl in which at least one piece ofhydrogen is replaced by fluorine or chlorine include fluoromethyl,2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl,6-fluorohexyl, 7-fluoroheptyl or 8-fluorooctyl. Further preferredexamples include 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl or5-fluoropentyl for increasing the dielectric anisotropy.

Specific examples of preferred alkenyl in which at least one piece ofhydrogen is replaced by fluorine or chlorine include 2,2-difluorovinyl,3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4-pentenylor 6,6-difluoro-5-hexenyl. Further preferred examples include2,2-difluorovinyl or 4,4-difluoro-3-butenyl for decreasing theviscosity.

Ring A and ring B are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine. Preferred ring Aor ring B is 1,4-cyclohexylene for decreasing the viscosity or forincreasing the maximum temperature, and 1,4-phenylene for decreasing theminimum temperature. With regard to a configuration of1,4-cyclohexylene, trans is preferred to cis for increasing the maximumtemperature. Tetrahydropyran-2,5-diyl includes:

preferably

Ring C and ring D are independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene. Preferred ring Cor ring D is 1,4-cyclohexylene for decreasing the viscosity or forincreasing the maximum temperature, and 1,4-phenylene for decreasing theminimum temperature.

Ring E and ring G are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine. Preferred ring Eor ring G is 1,4-cyclohexylene for decreasing the viscosity,tetrahydropyran-2,5-diyl for increasing the dielectric anisotropy, and1,4-phenylene for increasing the optical anisotropy. Ring F is2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene,2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl, or 7,8-difluorochroman-2,6-diyl.Preferred ring F is 2,3-difluoro-1,4-phenylene for decreasing theviscosity, and 2-chloro-3-fluoro-1,4-phenylene for decreasing theoptical anisotropy, and 7,8-difluorochroman-2,6-diyl for increasing thedielectric anisotropy.

Z¹, Z², Z⁴ and Z⁵ are in dependently a single bond, ethylene,carbonyloxy or methyleneoxy. Preferred Z¹, Z², Z⁴ or Z⁵ is a single bondfor decreasing the viscosity, ethylene for decreasing the minimumtemperature, and methyleneoxy for increasing the dielectric anisotropy.Z³ is a single bond, ethylene or carbonyloxy. Preferred Z³ is a singlebond for increasing the stability.

Then, a and b are independently 0, 1, 2 or 3, and a sum of a and b is 4or less. Preferred a is 1 for decreasing the viscosity, and 2 or 3 forincreasing the maximum temperature. Preferred b is 0 for decreasing theviscosity, and 1 for decreasing the minimum temperature. Then, cis 1, 2or 3. Preferred c is 1 for decreasing the viscosity, and 2 or 3 forincreasing the maximum temperature. Then, d is 1, 2 or 3, e is 0 or 1,and a sum of d and e is 3 or less. Preferred d is 1 for decreasing theviscosity, and 2 or 3 for increasing the maximum temperature. Preferrede is 0 for decreasing the viscosity, and 1 for decreasing the minimumtemperature.

In formula (4), P¹, P² and P³ are independently a polymerizable group.Preferred P¹, P² or P³ is a polymerizable group selected from the groupof groups represented by formula (P-1) to formula (P-6). Furtherpreferred P¹, P² or P³ is a group represented by formula (P-1), formula(P-2) or formula (P-3). Particularly preferred P¹, P² or P³ is a grouprepresented by formula (P-1) or formula (P-2). Most Preferred P¹, P² orP³ is a group represented by formula (P-1). A preferred grouprepresented by formula (P-1) is —OCO—CH═CH₂ or —OCO—C(CH₃)═CH₂. A wavyline in formula (P-1) to formula (P-6) represents a site to form abonding.

In formula (P-1) to formula (P-6), M¹, M² and M³ are independentlyhydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine. Preferred M¹, M² or M³ is hydrogen or methyl for increasingthe reactivity. Further preferred M¹ is hydrogen or methyl, and furtherpreferred M² or M³ is hydrogen.

Sp¹, Sp² and Sp³ are independently a single bond or alkylene having 1 to10 carbons, and in the alkylene, at least one piece of —CH₂— may bereplaced by —O—, —COO—, —OCO— or —OCOO—, and at least one piece of—CH₂—CH₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, atleast one piece of hydrogen may be replaced by fluorine or chlorine.Preferred Sp¹, Sp² or Sp³ is a single bond, —CH₂—CH₂—, —CH₂O—, —OCH₂—,—COO—, —OCO—, —CO—CH═CH— or —CH═CH—CO—. Further preferred Sp¹, Sp² orSp³ is a single bond.

In formula (4), when all of g pieces of P¹ and i pieces of P³ are thegroup represented by formula (P-4), at least one piece of g pieces ofSp¹ and i pieces of Sp³ is alkylene having 1 to 10 carbons in which atleast one piece of —CH₂— is replaced by —O—, —COO—, —OCO— or —OCOO—.

Ring I and ring K are independently cyclohexyl, cyclohexenyl, phenyl,1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl,pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one pieceof hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbonsin which at least one piece of hydrogen is replaced by fluorine orchlorine. Preferred ring I or ring K is phenyl. Ring J is1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene,naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl,naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl,naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl,naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl,pyrimidine-2,5-diyl or pyridine-2,5-diyl, and in the rings, at least onepiece of hydrogen may be replaced by fluorine, chlorine, alkyl having 1to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine. Preferred ring J is 1,4-phenylene or2-fluoro-1,4-phenylene.

Z⁶ and Z⁷ are independently a single bond or alkylene having 1 to 10carbons, and in the alkylene, at least one piece of —CH₂— may bereplaced by —O—, —CO—, —COO— or —OCO—, and at least one piece of—CH₂—CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—, —CH═C(CH₃)— or—C(CH₃)═C(CH₃)—, and in the groups, at least one piece of hydrogen maybe replaced by fluorine or chlorine. Preferred Z⁶ or Z⁷ is a singlebond, —CH₂—CH₂—, —CH₂O—, —OCH₂—, —COO— or —OCO—. Further preferred Z⁶ orZ⁷ is a single bond.

Then, f is 0, 1 or 2. Preferred f is 0 or 1. Then, g, h and i areindependently 0, 1, 2, 3 or 4, and a sum of g, h and i is 1 or more.Preferred g, h or i is 1 or 2.

Fifth, the preferred component compounds will be described. Preferredcompound (1) includes compound (1-1) to compound (1-12) described initem 2. In the compounds, at least one of the first componentspreferably includes compound (1-1), compound (1-2) or compound (1-8). Atleast two of the first components preferably includes a combination ofcompound (1-2) and compound (1-8).

Preferred compound (2) includes compound (2-1) to compound (2-13)described in item 5. In the compounds, at least one of the secondcomponents preferably includes compound (2-1), compound (2-3), compound(2-5), compound (2-6) or compound (2-7). At least two of the secondcomponents preferably include a combination of compound (2-1) andcompound (2-3), and a combination of compound (2-1) and compound (2-5).

Preferred compound (3) includes compound (3-1) to compound (3-22)described in item 8. In the compounds, at least one of the thirdcomponents preferably includes compound (3-1), compound (3-2), compound(3-3), compound (3-4), compound (3-6), compound (3-7), compound (3-8) orcompound (3-10). At least two of the third components preferably includea combination of compound (3-1) and compound (3-6), a combination ofcompound (3-1) and compound (3-10), a combination of compound (3-3) andcompound (3-6), a combination of compound (3-3) and compound (3-10), acombination of compound (3-4) and compound (3-6), or a combination ofcompound (3-4) and compound (3-10).

Preferred compound (4) includes compound (4-1) to compound (4-27)described in item 12. In the compounds, at least one of the additivecomponents preferably includes compound (4-1), compound (4-2), compound(4-24), compound (4-25), compound (4-26) or compound (4-27). At leasttwo of the additive components preferably include a combination ofcompound (4-1) and compound (4-2), a combination of compound (4-1) andcompound (4-18), a combination of compound (4-2) and compound (4-24), acombination of compound (4-2) and compound (4-25), a combination ofcompound (4-2) and compound (4-26), a combination of compound (4-25) andcompound (4-26), or a combination of compound (4-18) and compound(4-24).

Sixth, the additive that may be added to the composition will bedescribed. Such an additive includes the optically active compound, theantioxidant, the ultraviolet light absorber, the dye, the antifoamingagent, the polymerizable compound, the polymerization initiator and thepolymerization inhibitor. The optically active compound is added to thecomposition for the purpose of inducing a helical structure in theliquid crystal molecule to give a twist angle. Examples of such acompound include compound (5-1) to compound (5-5). A preferredproportion of the optically active compound is about 5% by weight orless. A further preferred proportion is in the range of about 0.01% byweight to about 2% by weight.

The antioxidant is added to the composition for preventing a decrease inthe specific resistance caused by heating in air, or for maintaining alarge voltage holding ratio at room temperature and also at thetemperature close to the maximum temperature even after the device hasbeen used for a long period of time. Specific examples of a preferredantioxidant include compound (6) in which n is an integer from 1 to 9.

In compound (6), preferred n is 1, 3, 5, 7 or 9. Further preferred n is7. Compound (6) in which n is 7 is effective in maintaining a largevoltage holding ratio at room temperature and also at the temperatureclose to the maximum temperature even after the device has been used fora long period of time because such compound (6) has a small volatility.A preferred proportion of the antioxidant is about 50 ppm or more forachieving an effect thereof, and about 600 ppm or less for avoiding adecrease in the maximum temperature or an increase in the minimumtemperature. A further preferred proportion is in the range of about 100ppm to about 300 ppm.

Specific examples of a preferred ultraviolet light absorber include abenzophenone derivative, a benzoate derivative and a triazolederivative. A light stabilizer such as an amine having steric hindranceis also preferred. A preferred proportion of the absorber and thestabilizer is about 50 ppm or more for achieving an effect thereof, andabout 10,000 ppm or less for avoiding a decrease in the maximumtemperature or an increase in the minimum temperature. A furtherpreferred proportion is in the range of about 100 ppm to about 10,000ppm.

A dichroic dye such as an azo dye or an anthraquinone dye is added tothe composition to be adapted for a device having a guest host (GH)mode. A preferred proportion of the dye is in the range of about 0.01%by weight to about 10% by weight. The antifoaming agent such as dimethylsilicone oil or methyl phenyl silicone oil is added to the compositionfor preventing foam formation. A preferred proportion of the antifoamingagent is about 1 ppm or more for achieving an effect thereof, and about1,000 ppm or less for preventing a poor display. A further preferredproportion is in the range of about 1 ppm to about 500 ppm.

The polymerizable compound is used to be adapted for a polymer sustainedalignment (PSA) mode device. Compound (4) is suitable for the purpose.Any other polymerizable compound that is different from compound (4) maybe added to the composition together with compound (4). Instead ofcompound (4), any other polymerizable compound that is different fromcompound (4) may be added to the composition. Specific examples of apreferred polymerizable compound include acrylate, methacrylate, a vinylcompound, a vinyloxy compound, propenyl ether, an epoxy compound(oxirane, oxetane) and vinyl ketone compound. Further preferred examplesinclude an acrylate derivative or a methacrylate derivative. A preferredproportion of compound (4) is about 10% by weight or more based on thetotal amount of the polymerizable compound. A further preferredproportion is about 50% by weight or more. A particularly preferredproportion is about 80% by weight or more. A most preferred proportionis 100% by weight.

The polymerizable compound such as compound (4) is polymerized byirradiation with ultraviolet light. The polymerizable compound may bepolymerized in the presence of a suitable initiator such as aphotopolymerization initiator. Suitable conditions for polymerization,suitable types of the initiator and suitable amounts thereof are knownto those skilled in the art and are described in literature. Forexample, Irgacure 651 (registered trademark; BASF), Irgacure 184(registered trademark; BASF) or Darocur 1173 (registered trademark;BASF), each being a photoinitiator, is suitable for radicalpolymerization. A preferred proportion of the photopolymerizationinitiator is in the range of about 0.1% by weight to about 5% by weightbased on the total amount of the polymerizable compound. A furtherpreferred proportion is in the range of about 1% by weight to about 3%by weight based thereon.

Upon storing the polymerizable compound such as compound (4), thepolymerization inhibitor may be added thereto for preventingpolymerization. The polymerizable compound is ordinarily added to thecomposition without removing the polymerization inhibitor. Specificexamples of the polymerization inhibitor include hydroquinone, ahydroquinone derivative such as methylhydroquinone, 4-t-butylcatechol,4-methoxyphenol and phenothiazine.

Seventh, the methods for synthesizing the component compounds will bedescribed. The compounds can be prepared according to known methods.Examples of the synthetic methods are described. The synthetic method ofcompound (1) is described in the section of Examples. Compound (2-1) isprepared according to a method described in JP S59-176221 A. Compound(3-6) is prepared according to a method described in JP 2000-53602 A.Compound (4-18) is prepared according to a method described in JPH7-101900 A. The antioxidant is commercially available. A compound inwhich w in formula (6) is 1 is available from Sigma-Aldrich Corporation.Compound (6) in which w is 7 or the like is prepared according to amethod described in U.S. Pat. No. 3,660,505 B.

Any compounds whose synthetic methods are not described above can beprepared according to the methods described in books such as OrganicSyntheses (John Wiley & Sons, Inc.), Organic Reactions (John Wiley &Sons, Inc.), Comprehensive Organic Synthesis (Pergamon Press) and NewExperimental Chemistry Course (Shin Jikken Kagaku Koza in Japanese)(Maruzen Co., Ltd.). The composition is prepared according to publiclyknown methods using the thus obtained compounds. For example, thecomponent compounds are mixed and dissolved in each other by heating.

Last, the application of the composition will be described. Most of thecomposition has the minimum temperature of about −10° C. or lower, themaximum temperature of about 70° C. or higher, and the opticalanisotropy in the range of about 0.07 to about 0.20. The compositionhaving optical anisotropy in the range of about 0.08 to about 0.25 maybe prepared by controlling the proportion of the component compounds orby mixing any other liquid crystal compound. Further the compositionhaving optical anisotropy in the range of about 0.10 to about 0.30 maybe prepared according to the method. A device including the compositionhas the large voltage holding ratio. The composition is suitable for usein the AM device. The composition is particularly suitable for use in atransmissive AM device. The composition can be used as the compositionhaving the nematic phase, and as the optically active composition byadding the optically active compound.

The composition can be used for the AM device. The composition can alsobe used for a PM device. The composition can also be used for the AMdevice and the PM device each having a mode such as the PC mode, the TNmode, the STN mode, the ECB mode, the OCB mode, the IPS mode, the FFSmode, the VA mode and the FPA mode. Use for the AM device having a modesuch as the TN mode, the OCB mode, the IPS mode and the FFS mode isparticularly preferred. In the AM device having the IPS mode or the FFSmode, alignment of liquid crystal molecules when no voltage is appliedmay be parallel or vertical to a glass substrate. The devices may be ofa reflective type, a transmissive type or a transflective type. Use forthe transmissive device is preferred. The composition can also be usedfor an amorphous silicon-TFT device or a polycrystal silicon-TFT device.The composition can also be used for a nematic curvilinear aligned phase(NCAP) device prepared by microencapsulating the composition, or for apolymer dispersed (PD) device in which a three-dimensionalnetwork-polymer is formed in the composition.

EXAMPLES

The invention will be described in greater detail by way of Examples.However, the invention is not limited by the Examples. The inventionincludes a mixture of a composition in Example 1 and a composition inExample 2. The invention also includes a mixture in which at least twocompositions in Examples were mixed. The thus prepared compound wasidentified by methods such as an NMR analysis. Characteristics of thecompound, the composition and the device were measured by methodsdescribed below.

NMR analysis: For measurement, DRX-500 made by Bruker BioSpinCorporation was used. In ¹H-NMR measurement, a sample was dissolved in adeuterated solvent such as CDCl₃, and measurement was carried out underconditions of room temperature, 500 MHz and 16 times of accumulation.Tetramethylsilane was used as an internal standard. In ¹⁹F-NMRmeasurement, CFCl₃ was used as an internal standard, and measurement wascarried out under conditions of 24 times of accumulation. In explainingnuclear magnetic resonance spectra obtained, s, d, t, q, quin, sex and mstand for a singlet, a doublet, a triplet, a quartet, a quintet, asextet and a multiplet, and br being broad, respectively.

Gas chromatographic analysis: For measurement, GC-14B Gas Chromatographmade by Shimadzu Corporation was used. A carrier gas was helium (2 mLper minute). A sample vaporizing chamber and a detector (FID) were setto 280° C. and 300° C., respectively. A capillary column DB-1 (length 30m, bore 0.32 mm, film thickness 0.25 μm; dimethylpolysiloxane as astationary phase; non-polar) made by Agilent Technologies, Inc. was usedfor separation of component compounds. After the column was kept at 200°C. for 2 minutes, the column was heated to 280° C. at a rate of 5° C.per minute. A sample was prepared in an acetone solution (0.1% byweight), and then 1 microliter of the solution was injected into thesample vaporizing chamber. A recorder was C-R5A Chromatopac made byShimadzu Corporation or the equivalent thereof. The resulting gaschromatogram showed a retention time of a peak and a peak areacorresponding to each of the component compounds.

As a solvent for diluting the sample, chloroform, hexane or the like mayalso be used. The following capillary columns may also be used forseparating component compounds: HP-1 (length 30 m, bore 0.32 mm, filmthickness 0.25 μm) made by Agilent Technologies, Inc., Rtx-1 (length 30m, bore 0.32 mm, film thickness 0.25 μm) made by Restek Corporation andBP-1 (length 30 m, bore 0.32 mm, film thickness 0.25 μm) made by SGEInternational Pty. Ltd. A capillary column CBP1-M50-025 (length 50 m,bore 0.25 mm, film thickness 0.25 μm) made by Shimadzu Corporation mayalso be used for the purpose of preventing an overlap of peaks of thecompounds.

A proportion of liquid crystal compounds contained in the compositionmay be calculated by the method as described below. The mixture ofliquid crystal compounds is detected by gas chromatograph (FID). An arearatio of each peak in the gas chromatogram corresponds to the ratio(weight ratio) of the liquid crystal compound. When the capillarycolumns described above were used, a correction coefficient of each ofthe liquid crystal compounds may be regarded as 1 (one). Accordingly,the proportion (% by weight) of the liquid crystal compounds can becalculated from the area ratio of each peak.

Sample for measurement: When characteristics of the composition and thedevice were measured, the composition was used as was. Upon measuringcharacteristics of a compound, a sample for measurement was prepared bymixing the compound (15% by weight) with a base liquid crystal (85% byweight). Values of characteristics of the compound were calculated,according to an extrapolation method, using values obtained bymeasurement. (Extrapolated value)={(measured value of asample)−0.85×(measured value of a base liquid crystal)}/0.15. When asmectic phase (or crystals) precipitates at the ratio thereof at 25° C.,a ratio of the compound to the base liquid crystal was changed step bystep in the order of (10% by weight: 90% by weight), (5% by weight: 95%by weight) and (1% by weight: 99% by weight). Values of maximumtemperature, optical anisotropy, viscosity and dielectric anisotropywith regard to the compound were determined according to theextrapolation method.

A base liquid crystal described below was used. A proportion of thecomponent compound was expressed in terms of weight percent (% byweight).

17.2%

27.6%

20.7%

20.7%

13.8%

Measuring method: Characteristics were measured according to the methodsdescribed below. Most of the measuring methods are applied as describedin the Standard of Japan Electronics and Information TechnologyIndustries Association (hereinafter abbreviated as JEITA) (JEITAED-2521B) discussed and established by JEITA, or modified thereon. Nothin film transistor (TFT) was attached to a TN device used formeasurement.

(1) Maximum temperature of the nematic phase (NI; ° C.): A sample wasplaced on a hot plate in a melting point apparatus equipped with apolarizing microscope, and heated at a rate of 1° C. per minute.Temperature when part of the sample began to change from a nematic phaseto an isotropic liquid was measured. A maximum temperature of thenematic phase may be occasionally abbreviated as “maximum temperature.”

(2) Minimum temperature of nematic phase (T_(c); ° C.): Samples eachhaving a nematic phase were put in glass vials and kept in freezers attemperatures of 0° C., −10° C., −20° C., −30° C. and −40° C. for 10days, and then liquid crystal phases were observed. For example, whenthe sample maintained the nematic phase at −20° C. and changed tocrystals or a smectic phase at −30° C., T_(c) was expressed asT_(c)<−20° C. A minimum temperature of the nematic phase may beoccasionally abbreviated as “minimum temperature.”

(3) Viscosity (bulk viscosity; η; measured at 20° C.; mPa·s): Formeasurement, a cone-plate (E type) rotational viscometer made by TokyoKeiki, Inc. was used.

(4) Viscosity (rotational viscosity; γ1; measured at 25° C.; mPa·s):Measurement was carried out according to the method described in M. Imaiet al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995).A sample was put in a VA device in which a distance (cell gap) betweentwo glass substrates was 20 micrometers. Voltage was applied stepwise tothe device in the range of 39 V to 50 V at an increment of 1 V. After aperiod of 0.2 second with no voltage application, voltage was repeatedlyapplied under conditions of only one rectangular wave (rectangularpulse; 0.2 second) and no voltage application (2 seconds). A peakcurrent and a peak time of transient current generated by the appliedvoltage were measured. A value of rotational viscosity was obtained fromthe measured values and calculation equation (8) described on page 40 ofthe paper presented by M. Imai et al. Dielectric anisotropy required forthe calculation was measured according to section (6) described below.

(5) Optical anisotropy (refractive index anisotropy; An; measured at 25°C.): Measurement was carried out by an Abbe refractometer with apolarizing plate mounted on an ocular, using light at a wavelength of589 nanometers. A surface of a main prism was rubbed in one direction,and then a sample was added dropwise onto the main prism. A refractiveindex (nμ) was measured when a direction of polarized light was parallelto a direction of rubbing. A refractive index (n⊥) was measured when thedirection of polarized light was perpendicular to the direction ofrubbing. A value of optical anisotropy was calculated from an equation:Δn=n∥−n⊥.

(6) Dielectric anisotropy (As; measured at 25° C.): A value ofdielectric anisotropy was calculated from an equation: Δε=ε∥−ε⊥. Adielectric constants (ε∥ and ε⊥) was measured as described below.

(1) Measurement of dielectric constant (ε∥): An ethanol (20 mL) solutionof octadecyltriethoxysilane (0.16 mL) was applied to a well-cleanedglass substrate. After rotating the glass substrate with a spinner, theglass substrate was heated at 150° C. for 1 hour. A sample was put in aVA device in which a distance (cell gap) between two glass substrateswas 4 micrometers, and the device was sealed with an ultraviolet-curableadhesive. Sine waves (0.5V, 1 kHz) were applied to the device, and after2 seconds, a dielectric constant (ε∥) of the liquid crystal molecules ina major axis direction was measured.

(2) Measurement of dielectric constant (ε⊥): A polyimide solution wasapplied to a well-cleaned glass substrate. After calcining the glasssubstrate, rubbing treatment was applied to the alignment film obtained.A sample was put in a TN device in which a distance (cell gap) betweentwo glass substrates was 9 micrometers and a twist angle was 80 degrees.Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2seconds, a dielectric constant (ε⊥) of the liquid crystal molecules in aminor axis direction was measured.

(7) Threshold voltage (Vth; measured at 25° C.; V): For measurement, anLCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used.Alight source was a halogen lamp. A sample was put in a normally blackmode VA device in which a distance (cell gap) between two glasssubstrates was 4 micrometers and a rubbing direction was anti-parallel,and the device was sealed with an ultraviolet-curable adhesive. Avoltage (60 Hz, rectangular waves) to be applied to the device wasstepwise increased from 0 V to 20 V at an increment of 0.02 V. On theoccasion, the device was irradiated with light from a directionperpendicular to the device, and an amount of light transmitted throughthe device was measured. A voltage-transmittance curve was prepared, inwhich the maximum amount of light corresponds to 100% transmittance andthe minimum amount of light corresponds to 0% transmittance. A thresholdvoltage is expressed in terms of a voltage at 10% transmittance.

(8) Voltage holding ratio (VHR-1; measured at 25° C.; %): A TN deviceused for measurement had a polyimide alignment film, and a distance(cell gap) between two glass substrates was 5 micrometers. A sample wasput in the device, and then the device was sealed with anultraviolet-curable adhesive. A pulse voltage (60 microseconds at 5 V)was applied to the TN device and the device was charged. A decayingvoltage was measured for 16.7 milliseconds with a high-speed voltmeter,and area A between a voltage curve and a horizontal axis in a unit cyclewas determined. Area B is an area without decay. A voltage holding ratiois expressed in terms of a percentage of area A to area B.

(9) Voltage holding ratio (VHR-2; measured at 80° C.; %): A voltageholding ratio was measured according to procedures identical with theprocedures described above except that measurement was carried out at80° C. in place of 25° C. The thus obtained value was expressed in termsof VHR-2.

(10) Voltage holding ratio (VHR-3; measured at 25° C.; %): Stability toultraviolet light was evaluated by measuring a voltage holding ratioafter a device was irradiated with ultraviolet light. A TN device usedfor measurement had a polyimide alignment film and a cell gap was 5micrometers. A sample was injected into the device, and then the devicewas irradiated with light for 20 minutes. A light source was an ultrahigh-pressure mercury lamp USH-500D (made by Ushio, Inc.), and adistance between the device and the light source was 20 centimeters. Inmeasurement of VHR-3, a decaying voltage was measured for 16.7milliseconds. A composition having large VHR-3 has a large stability toultraviolet light. A value of VHR-3 is preferably 90% or more, andfurther preferably 95% or more.

(11) Voltage holding ratio (VHR-4; measured at 25° C.; %): Stability toheat was evaluated by measuring a voltage holding ratio after a TNdevice into which a sample was injected was heated in aconstant-temperature bath at 80° C. for 500 hours. In measurement ofVHR-4, a decaying voltage was measured for 16.7 milliseconds. Acomposition having large VHR-4 has a large stability to heat.

(12) Response time (T; measured at 25° C.; ms): For measurement, anLCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used.A light source was a halogen lamp. A low-pass filter was set to 5 kHz. Asample was put in a normally black mode VA device in which a distance(cell gap) between two glass substrates was 4 micrometers and a rubbingdirection was anti-parallel. The device was sealed with anultraviolet-curable adhesive. A voltage (rectangular waves; 60 Hz, 10 V,0.5 second) was applied to the device. On the occasion, the device wasirradiated with light from a direction perpendicular to the device, andan amount of light transmitted through the device was measured. Themaximum amount of light corresponds to 100% transmittance and theminimum amount of light corresponds to 0% transmittance. A response timewas expressed in terms of time required for a change from 90%transmittance to 10% transmittance (fall time; millisecond).

(13) Specific resistance (p; measured at 25° C.; Ωcm): Into a vesselequipped with electrodes, 1.0 milliliter of a sample was injected. Adirect current voltage (10 V) was applied to the vessel, and a directcurrent after 10 seconds was measured. Specific resistance wascalculated from the following equation: (specificresistance)={(voltage)×(electric capacity of a vessel)}/{(directcurrent)×(dielectric constant of vacuum)}.

Compound (1-1) was prepared according to a method described below.

First Step:

Under a nitrogen atmosphere, compound (S-1) (40 g) and THF (300 mL) wereput in a reaction vessel, and cooled down to −74° C. Then, sec-butyllithium (1 M; n-hexane, a cyclohexane solution; 313 mL) was addeddropwise thereto, and further the resulting mixture was stirred for 2hours. Subsequently, sulfur powder (11.8 g) was added thereto andstirred for 2 hours while returning the resulting mixture to 25° C.Then, bromoacetaldehyde diethyl acetal (84 g) was added thereto, andsubjected to reflux for 2 hours. A reaction mixture was poured intowater, and the resulting reaction mixture was subjected to extractionwith toluene. An organic layer was washed with water, and dried overanhydrous magnesium sulfate. The solution was concentrated under reducedpressure, and a residue was purified by silica gel chromatography(toluene) to give (S-2) (31 g).

Second Step:

Under a nitrogen atmosphere, compound (S-2) (31 g), polyphosphoric acid(150 g) and toluene (250 mL) were put in a reaction vessel, andsubjected to reflux under heating for 3 hours. Then, a reaction mixturewas poured into water, and the resulting reaction mixture was subjectedto extraction with toluene. An organic layer was washed with water, anddried over anhydrous magnesium sulfate. The solution was concentratedunder reduced pressure, and a residue was purified by silica gelchromatography (toluene:heptane=2:3 in a volume ratio) to give (S-3)(12.9 g).

Third Step:

Under a nitrogen atmosphere, compound (S-3) (6 g) and THF (100 mL) wereput in a reaction vessel, and cooled down to −74° C. Then, LDA (1 M;n-hexane, a THF solution; 37 mL) was added dropwise thereto, and furtherthe resulting mixture was stirred for 2 hours. Subsequently, (S-4) (6 g)was added thereto and stirred for 2 hours while returning the resultingmixture to 25° C. A reaction mixture was poured into water, and theresulting reaction mixture was subjected to extraction with toluene. Anorganic layer was washed with water, and dried over anhydrous magnesiumsulfate to give (S-5). After then, a dehydration under addingP-toluenesulfonic acid thereto was performed according to a publiclyknown method described in the above scheme and to give (S-6), and ahydrogenation reaction and purification were performed with palladiumcarbon to give compound (1-1) (1.7 g). Moreover, if referring to Exampledescribed in WO2009159966 or the like, the dehydration and thehydrogenation reaction performed herein are easy to be implemented.

¹H-NMR (δ ppm; CDCl₃): 7.32 (d, 1H), 7.03 (t, 1H), 6.91 (d, 1H), 4.17(q, 2H), 2.78 (tt, 1H), 2.12 (dd, 2H), 1.88 (dd, 2H), 1.60-1.20 (m,10H), 0.91 (t, 3H).

Examples of composition were described below. The component compoundswere represented using symbols according to definitions in Table 3described below. In Table 3, the configuration of 1,4-cyclohexylene istrans. A parenthesized number next to a symbolized compound represents achemical formula to which the compound belongs. A symbol (—) means anyother liquid crystal compound. A proportion (percentage) of the liquidcrystal compound is expressed in terms of weight percent (% by weight)based on the weight of the liquid crystal composition containing noadditive. Values of the characteristics of the composition weresummarized in the last part.

TABLE 3 Method for Description of Compounds using Symbols R—(A₁)—Z₁— . .. . . —Z_(n)—(A_(n))—R′ 1) Left-terminal Group R— Symbol F—C_(n)H_(2n)—Fn- C_(n)H_(2n+1)— n- C_(n)H_(2n+1)O— nO- C_(m)H_(2m+1)OC_(n)H_(2n)—mOn- CH₂═CH— V— C_(n)H_(2n+1)—CH═CH— nV- CH₂═CH—C_(n)H_(2n)— Vn-C_(m)H_(2m+1)—CH═CH—C_(n)H_(2n)— mVn- CF₂═CH— VFF— CF₂═CH—C_(n)H_(2n)—VFFn- CH₂═CH—COO— AC— CH₂═C(CH₃)—COO— MAC— 2) Right-terminal Group —R′Symbol —C_(n)H_(2n+1) -n —OC_(n)H_(2n+1) —On —CH═CH₂ —V—CH═CH—C_(n)H_(2n+1) —Vn —C_(n)H_(2n)—CH═CH₂ -nV—C_(m)H_(2m)—CH═CH—C_(n)H_(2n+1) -mVn —CH═CF₂ —VFF —OCO—CH═CH₂ —AC—OCO—C(CH₃)═CH₂ —MAC 3) Bonding Group —Z_(n)— Symbol —C_(n)H_(2n)— n—COO— E —CH═CH— V —CH═CHO— VO —OCH═CH— OV —CH₂O— 1O —OCH₂— O1 4) Ring—A_(n)— Symbol

H

B

B(F)

B(2F)

B(F,F)

B(2F,5F)

B(2F,3F)

B(2F,3CL)

dh

Dh

ch

bt(7F)

Cro(7F,8F) 5) Examples of Description Example 1. 2O-bt(7F)H-3

Example 2. 2-BB(F)B-3

Example 3. V-HHB-1

Example 4. 3-HHB(2F,3F)-O2

Example 1

2O-bt(7F)B(2F)B-3 (1-8) 5% 2O-bt(7F)B(2F)B-5 (1-8) 5% 3-HH-V (2-1) 28% 3-HH-V1 (2-1) 5% 3-HHB-1 (2-5) 6% 3-HHB-3 (2-5) 3% V-HHB-1 (2-5) 6%3-HB(2F,3F)-O2 (3-1) 10%  3-BB(2F,3F)-O2 (3-4) 7% 5-BB(2F,3F)-O2 (3-4)7% 2-HHB(2F,3F)-O2 (3-6) 2% 3-HHB(2F,3F)-O2 (3-6) 7% 4-HHB(2F,3F)-O2(3-6) 2% V-HHB(2F,3F)-O2 (3-6) 7% NI = 88.3° C.; Tc < −20° C.; η = 16.5mPa · s; Δn = 0.118; Δε = −2.4.

Comparative Example 1

The composition in Example 1 contains compound (1) being a firstcomponent. Compound (1) has a negative dielectric anisotropy. Forcomparison, a composition in which the first component in Example 1 wasused in place of compound (3) having negative dielectric anisotropy wastaken as Comparative Example 1.

3-HH-V (2-1) 28%  3-HH-V1 (2-1) 5% 3-HHB-1 (2-5) 6% 3-HHB-3 (2-5) 3%V-HHB-1 (2-5) 6% 3-HB(2F,3F)-O2 (3-1) 10%  3-BB(2F,3F)-O2 (3-4) 7%5-BB(2F,3F)-O2 (3-4) 7% 2-HHB(2F,3F)-O2 (3-6) 2% 3-HHB(2F,3F)-O2 (3-6)7% 4-HHB(2F,3F)-O2 (3-6) 2% V-HHB(2F,3F)-O2 (3-6) 7% 2-BB(2F,3F)B-3(3-9) 3% 3-HBB(2F,3F)-O2 (3-10) 7% NI = 80.0° C.; Tc < −20° C.; η = 15.5mPa · s; Δn = 0.100; Δε = −2.6.

Example 2

2O-bt(7F)H-3 (1-1) 7% 2O-bt(7F)B(2F)B-3 (1-8) 3% 2-HH-3 (2-1) 12% 3-HH-4 (2-1) 9% 3-HH-O1 (2-1) 5% 3-HB-O2 (2-2) 3% 1-BB-3 (2-3) 3%VFF-HHB-1 (2-5) 3% V-HHB-1 (2-5) 6% 3-HBB-2 (2-6) 3% V-HBB-2 (2-6) 3%V-HB(2F,3F)-O2 (3-1) 5% 3-H2B(2F,3F)-O2 (3-2) 3% 2-H1OB(2F,3F)-O2 (3-3)5% 2O-BB(2F,3F)-O2 (3-4) 5% 3-HHB(2F,3F)-O2 (3-6) 5% V-HHB(2F,3F)-O2(3-6) 4% 5-HH2B(2F,3F)-O2 (3-7) 3% 2-HBB(2F,3F)-O2 (3-10) 3%3-HBB(2F,3F)-O2 (3-10) 4% 5-HBB(2F,3F)-O2 (3-10) 3%3-HEB(2F,3F)B(2F,3F)-O2 (3-11) 3% NI = 84.7° C.; Tc < −20° C.; η = 21.1mPa · s; Δn = 0.114; Δε = −2.9.

Example 3

2O-bt(7F)B-3 (1-2) 7% 2O-bt(7F)BB-3 (1-5) 1% 2O-bt(7F)BB-4 (1-5) 1%2O-bt(7F)BB-5 (1-5) 1% 3-HH-V (2-1) 19%  3-HH-V1 (2-1) 12%  2-BB(F)B-2V(2-7) 3% 3-HB(F)HH-2 (2-10) 4% V-HB(2F,3F)-O2 (3-1) 3% 3-HB(2F,3F)-O2(3-1) 10%  3-H1OB(2F,3F)-O2 (3-3) 4% 3-BB(2F,3F)-O2 (3-4) 10% 3-HHB(2F,3F)-O2 (3-6) 5% V-HHB(2F,3F)-O2 (3-6) 5% 3-HH1OB(2F,3F)-O2(3-8) 5% 3-HBB(2F,3F)-O2 (3-10) 10%  NI = 83.9° C.; Tc < −20° C.; η =21.6 mPa · s; Δn = 0.129; Δε = −3.5.

Example 4

2O-bt(7F)2H-3 (1-3) 3% 2O-bt(7F)B(2F)B-3 (1-8) 3% 2O-bt(7F)B(2F,3F)O1H-3(1-12) 1% 2O-bt(7F)B(2F,3F)O1H-4 (1-12) 1% 2O-bt(7F)B(2F,3F)O1H-5 (1-12)1% 2-HH-5 (2-1) 5% 3-HH-4 (2-1) 5% 3-HH-O1 (2-1) 5% 3-HH-V (2-1) 15% 3-HH-V1 (2-1) 7% 1-BB-5 (2-3) 3% 5-HB(2F,3F)-O2 (3-1) 13% 2-HHB(2F,3F)-O2 (3-6) 6% 3-HHB(2F,3F)-O2 (3-6) 10%  4-HHB(2F,3F)-O2(3-6) 5% 2-BB(2F,3F)B-3 (3-9) 4% 2-HBB(2F,3F)-O2 (3-10) 3%3-HBB(2F,3F)-O2 (3-10) 10%  NI = 90.6° C.; Tc <−20° C.; η = 21.2 mPa ·s; Δn = 0.110; Δε = −3.0.

Example 5

2O-bt(7F)HH-3 (1-4) 3% 2O-bt(7F)BB-3 (1-5) 1% 2O-bt(7F)BB-4 (1-5) 1%2O-bt(7F)BB-5 (1-5) 1% 2O-bt(7F)B(2F)B-3 (1-8) 3% 2-HH-3 (2-1) 15% 3-HH-V (2-1) 10%  3-HH-V1 (2-1) 10%  3-HB-O2 (2-2) 3% V-HHB-1 (2-5) 3%3-HB(2F,3F)-O2 (3-1) 6% 5-HB(2F,3F)-O2 (3-1) 8% 5-H2B(2F,3F)-O2 (3-2) 3%3-B(2F,3F)B(2F,3F)-O2 (3-5) 3% 2-HHB(2F,3F)-O2 (3-6) 8% 3-HHB(2F,3F)-O2(3-6) 9% 2-HBB(2F,3F)-O2 (3-10) 3% 3-HBB(2F,3F)-O2 (3-10) 10%  NI =88.2° C.; Tc <−20° C.; η = 21.8 mPa · s; Δn = 0.112; Δε = −3.3.

Example 6

3-HH1Obt(7F)-3 (1-6) 3% 2O-bt(7F)B(2F)B-3 (1-8) 5% 3-HH-V (2-1) 15% 5-HH-V (2-1) 10%  3-HH-V1 (2-1) 5% 7-HB-1 (2-2) 5% 2-BB(F)B-3 (2-7) 3%V-HB(2F,3F)-O2 (3-1) 4% 3-HB(2F,3F)-O2 (3-1) 10%  3-HHB(2F,3F)-O2 (3-6)10%  V-HHB(2F,3F)-O2 (3-6) 7% 2-HH1OB(2F,3F)-O2 (3-8) 3% 3-HBB(2F,3F)-O2(3-10) 8% 5-HBB(2F,3F)-O2 (3-10) 7% V-HBB(2F,3F)-O2 (3-10) 3%3-chB(2F,3F)-O2 (3-18) 2% NI = 92.9° C.; Tc <−20° C.; η = 22.1 mPa · s;Δn = 0.114; Δε = −3.3.

Example 7

2O-bt(7F)H-3 (1-1) 5% 2O-bt(7F)B(2F)B-3 (1-8) 5% 2-HH-3 (2-1) 6% 2-HH-5(2-1) 7% 3-HH-V (2-1) 16%  3-HH-V1 (2-1) 5% 1-BB-3 (2-3) 3% 5-HBB(F)B-3(2-13) 3% 3-HB(2F,3F)-O2 (3-1) 9% 5-HB(2F,3F)-O2 (3-1) 10% V-HHB(2F,3F)-O2 (3-6) 10%  3-HBB(2F,3F)-O2 (3-10) 10%  5-HBB(2F,3F)-O2(3-10) 6% 3-HDhB(2F,3F)-O2 (3-16) 5% NI = 86.7° C.; Tc <−20° C.; η =21.5 mPa · s; Δn = 0.113; Δε = −3.3.

Example 8

2O-bt(7F)B-3 (1-2) 3% 2O-bt(7F)HH-3 (1-4) 3% 2O-bt(7F)BB-3 (1-5) 1%2O-bt(7F)BB-4 (1-5) 1% 2O-bt(7F)BB-5 (1-5) 1% 3-HH-V (2-1) 20%  3-HH-V1(2-1) 13%  V-HHB-1 (2-5) 3% V-HBB-3 (2-6) 3% 3-HB(2F,3F)-O2 (3-1) 10% 2-H1OB(2F,3F)-O2 (3-3) 3% 3-BB(2F,3F)-O2 (3-4) 5% 5-BB(2F,3F)-O2 (3-4)5% V-HH1OB(2F,3F)-O2 (3-8) 3% 3-HBB(2F,3F)-O2 (3-10) 6% 5-HBB(2F,3F)-O2(3-10) 6% 3-HEB(2F,3F)B(2F,3F)-O2 (3-11) 8% V-chB(2F,3F)-O2 (3-18) 3%5-HchB(2F,3F)-O2 (3-19) 3% NI = 84.0° C.; Tc <−20° C.; η = 22.6 mPa · s;Δn = 0.126; Δε = −3.6.

Example 9

2O-bt(7F)B-3 (1-2) 5% 2O-bt(7F)B(2F)B-3 (1-8) 5% 3-HH-V (2-1) 20% 3-HH-V1 (2-1) 10%  3-HB-O2 (2-2) 6% 3-HHEH-3 (2-4) 3% 3-HHEH-5 (2-4) 3%3-H2B(2F,3F)-O2 (3-2) 6% 3-BB(2F,3F)-O2 (3-4) 5% 2O-BB(2F,3F)-O2 (3-4)6% 2-HHB(2F,3F)-O2 (3-6) 5% 3-HHB(2F,3F)-O2 (3-6) 5% V-HHB(2F,3F)-O2(3-6) 10%  3-HBB(2F,3F)-O2 (3-10) 8% V2-HchB(2F,3F)-O2 (3-19) 3% NI =95.1° C.; Tc <−20° C.; η = 19.6 mPa · s; Δn = 0.123; Δε = −3.2.

Example 10

2O-bt(7F)H-3 (1-1) 5% 1V2-HH-2V1 (2-1) 3% 3-HH-V (2-1) 24%  3-HH-V1(2-1) 9% 5-HB-O2 (2-2) 4% 3-HBB-2 (2-6) 5% 3-HB(2F,3F)-O2 (3-1) 6%5-HB(2F,3F)-O2 (3-1) 5% 2O-BB(2F,3F)-O2 (3-4) 5% 2-HHB(2F,3F)-O2 (3-6)6% 3-HHB(2F,3F)-O2 (3-6) 10%  3-HBB(2F,3F)-O2 (3-10) 12% 3-BB(2F)B(2F,3F)-O2 (3-20) 3% 1O1-HBBH-5 (—) 3% NI = 93.6° C.; Tc <−20°C.; η = 17.0 mPa · s; Δn = 0.109; Δε = −2.8.

Example 11

2O-bt(7F)2H-3 (1-3) 3% 2O-bt(7F)HH-3 (1-4) 3% 2O-bt(7F)B(2F,3F)-O2 (1-9)1% 2O-bt(7F)B(2F,3F)-O3 (1-9) 1% 2O-bt(7F)B(2F,3F)-O4 (1-9) 1% 3-HH-V(2-1) 18%  5-HH-V (2-1) 10%  3-HH-V1 (2-1) 5% 1-BB-5 (2-3) 5% 5-B(F)BB-2(2-8) 5% V2-BB2B-1 (2-9) 5% 3-HB(2F,3F)-O2 (3-1) 8% 2-HHB(2F,3F)-O2(3-6) 6% 3-HHB(2F,3F)-O2 (3-6) 10%  3-HH2B(2F,3F)-O2 (3-7) 3%3-HBB(2F,3F)-O2 (3-10) 6% 3-HEB(2F,3F)B(2F,3F)-O2 (3-11) 3%3-HDhB(2F,3F)-O2 (3-16) 7% NI = 94.2° C.; Tc <−20° C.; η = 20.6 mPa · s;Δn = 0.116; Δε = −3.0.

Example 12

2O-bt(7F)B(2F)B-3 (1-8) 5% 2O-bt(7F)B(2F,3F)O1H-3 (1-12) 1%2O-bt(7F)B(2F,3F)O1H-4 (1-12) 1% 2O-bt(7F)B(2F,3F)O1H-5 (1-12) 1% 2-HH-3(2-1) 7% 5-HH-O1 (2-1) 3% 3-HH-V (2-1) 10%  5-HH-V (2-1) 7% 3-HH-V1(2-1) 10%  3-HHB-1 (2-5) 3% 3-HB(2F,3F)-O2 (3-1) 13%  3-BB(2F,3F)-O2(3-4) 10%  2-HHB(2F,3F)-O2 (3-6) 6% 3-HHB(2F,3F)-O2 (3-6) 10% V-HBB(2F,3F)-O2 (3-10) 10%  5-HHB(2F,3CL)-O2 (3-12) 3% NI = 84.4° C.; Tc<−20° C.; η = 20.6 mPa · s; Δn = 0.111; Δε = −3.1.

Example 13

2O-bt(7F)B(2F)B-3 (1-8) 5% 2O-bt(7F)B(2F)B-5 (1-8) 5% 2-HH-3 (2-1) 23% 2-HH-5 (2-1) 12%  3-HH-VFF (2-1) 5% V-HBB-2 (2-6) 5% 5-HB(2F,3F)-O2(3-1) 5% 2-H1OB(2F,3F)-O2 (3-3) 3% 3-H1OB(2F,3F)-O2 (3-3) 3%V-HHB(2F,3F)-O2 (3-6) 7% 3-HH1OB(2F,3F)-O2 (3-8) 7% 2-BB(2F,3F)B-3 (3-9)3% 3-H1OCro(7F,8F)-5 (3-14) 3% 3-HDhB(2F,3F)-O2 (3-16) 5%3-HchB(2F,3F)-O2 (3-19) 6% 5-BB(2F)B(2F,3F)-O2 (3-20) 3% NI = 87.1° C.;Tc <−20° C.; η = 23.4 mPa · s; Δn = 0.115; Δε = −3.1.

Example 14

2O-bt(7F)H-3 (1-1) 6% 2O-bt(7F)B(2F)B-3 (1-8) 4% 2-HH-5 (2-1) 8% 3-HH-4(2-1) 10%  3-HH-V1 (2-1) 14%  V2-BB-1 (2-3) 5% 3-HHB-O1 (2-5) 5%3-HB(2F,3F)-O2 (3-1) 9% 5-HB(2F,3F)-O2 (3-1) 7% 3-HHB(2F,3F)-O2 (3-6)10%  4-HHB(2F,3F)-O2 (3-6) 3% V-HHB(2F,3F)-O2 (3-6) 7% 3-HBB(2F,3F)-O2(3-10) 9% 3-HBB(2F,3CL)-O2 (3-13) 3% NI = 96.7° C.; Tc <−20° C.; η =20.6 mPa · s; Δn = 0.110; Δε = −3.2.

Example 15

2O-bt(7F)B-3 (1-2) 5% 2O-bt(7F)B(2F,3F)-O2 (1-9) 1% 2O-bt(7F)B(2F,3F)-O3(1-9) 1% 2O-bt(7F)B(2F,3F)-O4 (1-9) 1% 3-HH-V (2-1) 20%  3-HH-V1 (2-1)10%  F3-HH-V (2-1) 3% V-HHB-1 (2-5) 5% V2-HHB-1 (2-5) 5% 3-HHEBH-3(2-11) 3% V-HB(2F,3F)-O2 (3-1) 5% 3-HB(2F,3F)-O2 (3-1) 5% 5-HB(2F,3F)-O2(3-1) 4% 2-HHB(2F,3F)-O2 (3-6) 2% 3-HHB(2F,3F)-O2 (3-6) 7%4-HHB(2F,3F)-O2 (3-6) 2% V-HHB(2F,3F)-O2 (3-6) 7% 2-BB(2F,3F)B-4 (3-9)3% 3-HBB(2F,3F)-O2 (3-10) 5% 5-HBB(2F,3CL)-O2 (3-13) 3%3-H1OCro(7F,8F)-5 (3-14) 3% NI = 95.3° C.; Tc <−20° C.; η = 20.0 mPa ·s; Δn = 0.110; Δε = −3.0.

Example 16

2O-bt(7F)B-3 (1-2) 3% 2O-bt(7F)B(2F)B-3 (1-8) 3% 2O-bt(7F)B(2F,3F)O1H-3(1-12) 1% 2O-bt(7F)B(2F,3F)O1H-4 (1-12) 1% 2O-bt(7F)B(2F,3F)O1H-5 (1-12)1% 3-HH-V (2-1) 29%  3-HHB-1 (2-5) 6% VFF2-HHB-1 (2-5) 3% 5-HBB(F)B-2(2-13) 3% 3-HB(2F,3F)-O2 (3-1) 12%  3-BB(2F,3F)-O2 (3-4) 10% 2-HHB(2F,3F)-O2 (3-6) 3% 3-HHB(2F,3F)-O2 (3-6) 10%  V-HHB(2F,3F)-O2(3-6) 9% 3-HH1OCro(7F,8F)-5 (3-15) 3% 3-BB(F)B(2F,3F)-O2 (3-21) 3% NI =91.2° C.; Tc <−20° C.; η = 22.4 mPa · s; Δn = 0.118; Δε = −3.0.

Example 17

2O-bt(7F)B(2F)B-3 (1-8) 5% 2O-bt(7F)B(2F)B-5 (1-8) 5% 2-HH-3 (2-1) 25% 3-HH-4 (2-1) 10%  3-HHEH-5 (2-4) 3% 3-HHEBH-5 (2-11) 3% V-HB(2F,3F)-O2(3-1) 10%  3-HB(2F,3F)-O2 (3-1) 5% 3-BB(2F,3F)-O2 (3-4) 4%5-BB(2F,3F)-O2 (3-4) 4% 3-HHB(2F,3F)-O2 (3-6) 7% V-HHB(2F,3F)-O2 (3-6)5% 2-HBB(2F,3F)-O2 (3-10) 8% 3-HBB(2F,3F)-O2 (3-10) 3% 3-dhBB(2F,3F)-O2(3-17) 3% NI = 86.8° C.; Tc <−20° C.; η = 22.8 mPa · s; Δn = 0.115; Δε =−2.9.

Example 18

2O-bt(7F)H-3 (1-1) 5% 2O-bt(7F)B(2F)B-3 (1-8) 5% 2-HH-3 (2-1) 17% 3-HH-V (2-1) 11%  1V2-BB-1 (2-3) 3% V-HHB-1 (2-5) 6% 5-HB(F)BH-3 (2-12)3% 3-HB(2F,3F)-O2 (3-1) 13%  3-HH2B(2F,3F)-O2 (3-7) 3% 5-HH2B(2F,3F)-O2(3-7) 5% V-HH1OB(2F,3F)-O2 (3-8) 10%  2-BB(2F,3F)B-3 (3-9) 4%4-HBB(2F,3F)-O2 (3-10) 3% 3-HEB(2F,3F)B(2F,3F)-O2 (3-11) 3%3-HHB(2F,3CL)-O2 (3-12) 3% 3-HchB(2F,3F)-O2 (3-19) 3% 5-HchB(2F,3F)-O2(3-19) 3% NI = 94.5° C.; Tc <−20° C.; η = 22.1 mPa · s; Δn = 0.113; Δε =−3.0.

The maximum temperature (NI) of nematic phase and optical anisotropy(Δn) of the composition in Comparative Example 1 were 80.0° C. and0.100, respectively. On the other hand, the maximum temperature ofnematic phase and optical anisotropy of the composition in Example 1were 88.3° C. and 0.118, respectively. Thus, the composition in Exampleswere found to have a higher maximum temperature of nematic phase and alarger optical anisotropy in comparison with the composition inComparative Examples. Accordingly, the liquid crystal composition of theinvention is concluded to have superb characteristics.

INDUSTRIAL APPLICABILITY

A liquid crystal composition of the invention satisfies at least one ofcharacteristics such as a high maximum temperature, a low minimumtemperature, a small viscosity, a large optical anisotropy, a largenegative dielectric anisotropy, a large specific resistance, a highstability to ultraviolet light and a high stability to heat, or has asuitable balance regarding at least two of the characteristics. A liquidcrystal display device including the composition has characteristicssuch as a short response time, a large voltage holding ratio, a lowthreshold voltage, a large contrast ratio, a long service life and soforth, and thus can be used for a liquid crystal projector, a liquidcrystal television and so forth.

What is claimed is:
 1. A liquid crystal composition that has a nematicphase and a negative dielectric anisotropy, and contains at least onecompound selected from the group of compounds represented by formula (1)as a first component and at least one compound selected from the groupof compounds represented by formula (2) as a second component:

wherein, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring A and ring B are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine; Z¹ and Z² areindependently a single bond, ethylene, carbonyloxy or methyleneoxy; aand b are independently 0, 1, 2 or 3; and a sum of a and b is 4 or less,and wherein, in formula (2), R³ and R⁴ are independently alkyl having 1to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkyl having 1 to 12 carbons in which at least one piece ofhydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring C and ring D are independently 1,4-cyclohexylene,1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z³is a single bond, ethylene or carbonyloxy; and c is 1, 2 or
 3. 2. Theliquid crystal composition according to claim 1, containing at least onecompound selected from the group of compounds represented by formula(1-1) to formula (1-12) as the first component:

wherein, in formula (1-1) to formula (1-12), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.
 3. The liquid crystal compositionaccording to claim 1, wherein a proportion of the first component is inthe range of 3% by weight to 30% by weight based on the total amount ofthe liquid crystal composition.
 4. The liquid crystal compositionaccording to claim 1, containing at least one compound selected from thegroup of compounds represented by formula (2-1) to formula (2-13) as thesecond component:

wherein, in formula (2-1) to formula (2-13), R³ and R⁴ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkyl having 1 to 12 carbons in which at leastone piece of hydrogen is replaced by fluorine or chlorine, or alkenylhaving 2 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.
 5. The liquid crystal compositionaccording to claim 1, wherein a proportion of the second component is inthe range of 15% by weight to 80% by weight based on the total amount ofthe liquid crystal composition.
 6. The liquid crystal compositionaccording to claim 1, containing at least one compound selected from thegroup of compounds represented by formula (3) as a third component:

wherein, in formula (3), R⁵ and R⁶ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one piece of hydrogen is replaced by fluorineor chlorine; ring E and ring G are independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,1,4-phenylene in which at least one piece of hydrogen is replaced byfluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl inwhich at least one piece of hydrogen is replaced by fluorine orchlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least onepiece of hydrogen is replaced by fluorine or chlorine; ring F is2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene,2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl, or 7,8-difluorochroman-2,6-diyl; Z⁴and Z⁵ are independently a single bond, ethylene, carbonyloxy ormethyleneoxy; d is 1, 2 or 3; e is 0 or 1; and a sum of d and e is 3 orless.
 7. The liquid crystal composition according to claim 6, containingat least one compound selected from the group of compounds representedby formula (3-1) to formula (3-22) as the third component:

wherein, in formula (3-1) to formula (3-22), R⁵ and R⁶ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine.
 8. The liquid crystal compositionaccording to claim 6, wherein a proportion of the third component is inthe range of 10% by weight to 80% by weight based on the total amount ofthe liquid crystal composition.
 9. The liquid crystal compositionaccording to claim 1, containing at least one polymerizable compoundselected from the group of compounds represented by formula (4) as anadditive component:

wherein, in formula (4), ring I and ring K are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, atleast one piece of hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one piece of hydrogen is replaced byfluorine or chlorine; ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthe rings, at least one piece of hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one piece of hydrogenis replaced by fluorine or chlorine; Z⁶ and Z⁷ are independently asingle bond or alkylene having 1 to 10 carbons, and in the alkylene, atleast one piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—,and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—,—C(CH₃)═CH—, —CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in the groups, at leastone piece of hydrogen may be replaced by fluorine or chlorine; P¹, P²and P³ are independently a polymerizable group; Sp¹, Sp² and Sp³ areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or —C≡C—, and in the groups, at least one piece of hydrogen maybe replaced by fluorine or chlorine; f is 0, 1 or 2; g, h and i areindependently 0, 1, 2, 3 or 4; and a sum of g, h and i is 1 or more. 10.The liquid crystal composition according to claim 9, wherein, in formula(4), P¹, P² and P³ are independently a polymerizable group selected fromthe group of groups represented by formula (P-1) to formula (P-6):

wherein, in formula (P-1) to formula (P-6), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine; in formula (4), when all of g piecesof P¹ and i pieces of P³ are the group represented by formula (P-4), atleast one piece of g pieces of Sp′ and i pieces of Sp³ is alkylene inwhich at least one piece of —CH₂— is replaced by —O—, —COO—, —OCO— or—OCOO—.
 11. The liquid crystal composition according to claim 9,containing at least one polymerizable compound selected from the groupof compounds represented by formula (4-1) to formula (4-27) as theadditive component:

wherein, in formula (4-1) to formula (4-27), P⁴, P⁵ and P⁶ areindependently a polymerizable group selected from the group of groupsrepresented by formula (P-1) to formula (P-3);

wherein, in formula (P-1) to formula (P-3), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one piece of hydrogen isreplaced by fluorine or chlorine; and in formula (4-1) to formula(4-27), Sp¹, Sp² and Sp^(a) are independently a single bond or alkylenehaving 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂—may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one pieceof —CH₂—CH₂— may be replaced by —CH═CH— or and in the groups, at leastone piece of hydrogen may be replaced by fluorine or chlorine.
 12. Theliquid crystal composition according to claim 6, containing at least onepolymerizable compound selected from the group of compounds representedby formula (4) as an additive component:

wherein, in formula (4), ring I and ring K are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, atleast one piece of hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one piece of hydrogen is replaced byfluorine or chlorine; ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthe rings, at least one piece of hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one piece of hydrogenis replaced by fluorine or chlorine; Z⁶ and Z⁷ are independently asingle bond or alkylene having 1 to 10 carbons, and in the alkylene, atleast one piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—,and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—,—C(CH₃)═CH—, —CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in the groups, at leastone piece of hydrogen may be replaced by fluorine or chlorine; P¹, P²and P³ are independently a polymerizable group; Sp¹, Sp² and Sp^(a) areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or —C≡C—, and in the groups, at least one piece of hydrogen maybe replaced by fluorine or chlorine; f is 0, 1 or 2; g, h and i areindependently 0, 1, 2, 3 or 4; and a sum of g, h and i is 1 or more. 13.The liquid crystal composition according to claim 9, wherein aproportion of the additive component is the range of 0.03% by weight to10% by weight based on the total amount of the liquid crystalcomposition.
 14. A liquid crystal display device, including the liquidcrystal composition according to claim
 1. 15. The liquid crystal displaydevice according to claim 14, wherein an operating mode in the liquidcrystal display device includes an IPS mode, a VA mode, an FFS mode oran FPA mode, and a driving mode in the liquid crystal display deviceincludes an active matrix mode.
 16. A polymer sustained alignment modeliquid crystal display device, wherein the liquid crystal display deviceincludes the liquid crystal composition according to claim 9, or thepolymerizable compound in the liquid crystal composition is polymerized.